EP0133088B1 - Procédé de préparation d'additifs détergents-dispersants de très haute alcalinité à base de calcium et produits ainsi obtenus - Google Patents
Procédé de préparation d'additifs détergents-dispersants de très haute alcalinité à base de calcium et produits ainsi obtenus Download PDFInfo
- Publication number
- EP0133088B1 EP0133088B1 EP84401440A EP84401440A EP0133088B1 EP 0133088 B1 EP0133088 B1 EP 0133088B1 EP 84401440 A EP84401440 A EP 84401440A EP 84401440 A EP84401440 A EP 84401440A EP 0133088 B1 EP0133088 B1 EP 0133088B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ranging
- process according
- glycol
- lime
- alkylphenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000654 additive Substances 0.000 title claims abstract description 11
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title abstract description 6
- 229910052791 calcium Inorganic materials 0.000 title abstract description 6
- 239000011575 calcium Substances 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 59
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims abstract description 22
- 235000011941 Tilia x europaea Nutrition 0.000 claims abstract description 22
- 239000004571 lime Substances 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 halogen ions Chemical class 0.000 claims abstract description 16
- 239000003921 oil Substances 0.000 claims abstract description 14
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 239000010687 lubricating oil Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000000996 additive effect Effects 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 230000001050 lubricating effect Effects 0.000 claims 1
- 229910001510 metal chloride Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 20
- 239000013049 sediment Substances 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 12
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 239000007788 liquid Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- UENOQWSWMYJKIW-UHFFFAOYSA-N 1,2,2-trimethylcyclohexan-1-ol Chemical compound CC1(C)CCCCC1(C)O UENOQWSWMYJKIW-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010711 gasoline engine oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
Definitions
- the present invention relates to a process for the preparation of detergent-dispersant additives of very high alkalinity for lubricating oils as well as the products obtained.
- An improved variant of said process consists in carrying out the first step in the presence of an optionally hydroxylated C 1 -C 4 carboxylic acid such as formic acid, acetic acid, glycolic acid or oxalic acid.
- alkyl benzene sulfonic acids acids obtained by the sulfonation of alkylbenzenes having or alk y radicals contain from 15 to 30 carbon atoms and are derived from linear olefins or olefin oligomers, as well as those obtained by sulfonation of petroleum fractions; their molecular mass expressed as sodium salt generally corresponds to a value of 430 to 560. They are generally used in solution at around 70% in dilution oil.
- alkylphenols means alkylphenols carrying one or more C 9 -C 15 alkyl substituents and preferably nonyl, decyl, dodecyl or tetradecylphenols.
- paraffinic oils such as 100 Neutral oil, as well as naphthenic or mixed oils.
- the amount of oil favorably used is such that the amount of oil contained in the final product (including that coming from the starting alkylbenzene sulfonic acid) represents from 20 to 60% by weight of said product, preferably 25 at 55% and very particularly from 30 to 40% by weight of said product.
- halide ions mention may preferably be made of CI-; they are used by means of ammonium or metal salts such as ammonium chloride, calcium chloride, zinc chloride ...
- This first step during which the alkylbenzene sulfonic acid is transformed into neutral alkylbenzene sulfonate, can last from a few minutes to 1 hour and generally of the order of half an hour.
- the step of removing the water formed is generally carried out at a temperature of 110-150 ° C and preferably 130-140 ° C.
- C 6 -C 14 alkanols or cycloalkanols such as ethylhexanol , alcohols oxo, decyl alcohol, tridecyl alcohol, trimethylcyclohexanol ...
- ethers of alkylene glycols such as butoxy-2 ethanol, butoxy-2 propanol, hexyloxy-2 ethanol, methyl ethers of dipropylene glycol
- alkylene glycols such as propylene glycol, hexylene glycol; butanediols.
- the glycol and the heavy alcohol can be introduced in full at the start of the third stage or preferably by fraction during the third stage.
- the sulfur necessary for sulfurization can be introduced at the start of the third stage or else it can already be present in the first stage.
- the sulfurization operation is carried out at a temperature ranging from 160 ° C. to a temperature below the boiling point of heavy alcohol at normal pressure or under slight depression; it usually lasts 1 to 2 hours.
- the carbonation operation is favorably carried out at a temperature ranging from 160 ° C. to a temperature lower than that of boiling of the heavy alcohol, for a period which can range from 1 to 4 hours and generally about 2 hours; the amount of C0 2 introduced is between that which can be completely absorbed by the reaction medium and an excess of 30% of this amount.
- this carbonation operation can be carried out in the presence of an additional quantity of fresh glycol to compensate for the glycol which may be vaporized.
- the fifth step is preferably carried out under vacuum at a temperature of 160-220 ° C in about one hour.
- the present invention also relates to detergents-dispersants of high alkalinity based on calcium obtained by the process described above.
- the amount of TBN 350 detergent-dispersant that can be added to lubricating oils is generally between 1.5 and 2% for a gasoline engine oil, between 3 and 4% for a diesel engine oil and between 7 and 20% for a marine engine oil.
- the lubricating oils which can thus be improved can be chosen from a wide variety of lubricating oils, such as naphthenic, paraffinic and mixed base lubricating oils, other hydrocarbon lubricants, for example lubricating oils derived from products.
- hard coal and synthetic oils for example alkylene polymers, alkylene oxide type polymers and their derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxide in the presence water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids, liquid esters of liquid acids of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkyl biphenyl ethers, polymers silicon.
- Additional additives may also be present in said lubricating oils alongside the detergent-dispersants obtained according to the process of the invention; we can cite for example antioxidant additives, anti-corrosion, ashless dispersant additives ...
- the mixture is heated at 90 ° C for 30 minutes.
- glycol and a fraction of butylglycol are added over ten minutes, then the remainder of butylglycol over fifty minutes. It is heated to 160 ° C under slight vacuum for 1 hour.
- the vacuum is gradually tightened to 66.5 X 10 2 Pa and then heated to 200 ° C for 1 hour.
- the finished product is added to a SAE 50 oil with a paraffinic tendency so as to obtain a solution containing 25% of additive.
- the amounts of reagents used are those used in Example 1.
- the mixture is heated to 90 ° C. and then sulfur and ammonium chloride are added.
- glycol and a fraction of butylglycol are heated in twenty minutes and then the rest of the butylglycol in 1 hour.
- the mixture is heated to 165 ° C. and then carbonated for 2 hours at atmospheric pressure.
- Example 21 The operation described in Example 21 is carried out by replacing the 18 g of acetic acid with 13.8 g of formic acid.
- Example 1 The operation described in Example 1 is carried out by replacing the (100 + 560 g) of butylglycol with a mixture of (100 + 193 g) of 1,4-butanediol and of (100 + 400 g) of 2-ethylhexanol and decreasing the amount of glycol.
- the results obtained are shown in Table VI.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT84401440T ATE27298T1 (de) | 1983-07-11 | 1984-07-06 | Verfahren zur herstellung von auf calcium basierten detergenz-dispergierzusaetzen mit sehr hoher alkalitaet und die erhaltenen produkte. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8311494 | 1983-07-11 | ||
| FR8311494A FR2549080B1 (fr) | 1983-07-11 | 1983-07-11 | Procede de preparation d'additifs detergents-dispersants de tres haute alcalinite a base de calcium et additifs detergents-dispersants pour huiles lubrifiantes ainsi obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0133088A1 EP0133088A1 (fr) | 1985-02-13 |
| EP0133088B1 true EP0133088B1 (fr) | 1987-05-20 |
Family
ID=9290698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP84401440A Expired EP0133088B1 (fr) | 1983-07-11 | 1984-07-06 | Procédé de préparation d'additifs détergents-dispersants de très haute alcalinité à base de calcium et produits ainsi obtenus |
Country Status (18)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2584414B1 (fr) * | 1985-07-08 | 1987-10-30 | Orogil | Nouveaux additifs detergents-dispersants sulfones et sulfurises pour huiles lubrifiantes |
| NZ221128A (en) * | 1986-08-08 | 1989-09-27 | Chevron Res | Overbased sulphurised alkylphenols as lube oil additives |
| US5714443A (en) * | 1986-11-29 | 1998-02-03 | Bp Chemicals (Additives) Limited | Sulphurised alkaline earth metal hydrocarbyl phenates, their production and use thereof |
| GB8628609D0 (en) * | 1986-11-29 | 1987-01-07 | Bp Chemicals Additives | Lubricating oil additives |
| US5716914A (en) * | 1986-11-29 | 1998-02-10 | Bp International Limited | Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof |
| US4780224A (en) * | 1987-12-07 | 1988-10-25 | Texaco Inc. | Method of preparing overbased calcium sulfonates |
| US4810396A (en) * | 1988-04-29 | 1989-03-07 | Texaco Inc. | Process for preparing overbased calcium sulfonates |
| GB8814012D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Chemical process |
| GB8814009D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Lubricating oil additives |
| GB8814013D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Chemical process |
| GB8814010D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Addivites Ltd | Lubricating oil additives |
| US4879053A (en) * | 1988-07-11 | 1989-11-07 | Texaco Inc. | Process for preparing overbased calcium sulfonates |
| AU638705B2 (en) * | 1989-04-20 | 1993-07-08 | Lubrizol Corporation, The | Methods for reducing friction between relatively slideable components using metal overbased colloidal disperse systems |
| GB2232665A (en) * | 1989-05-31 | 1990-12-19 | Exxon Chemical Patents Inc | Sulphonic acid derivatives and their use as emulsifiers |
| GB8917094D0 (en) * | 1989-07-26 | 1989-09-13 | Bp Chemicals Additives | Chemical process |
| US4929373A (en) * | 1989-10-10 | 1990-05-29 | Texaco Inc. | Process for preparing overbased calcium sulfonates |
| US5259966A (en) * | 1992-11-10 | 1993-11-09 | The Lubrizol Corporation | Low chlorine overbased calcium salts |
| US5401424A (en) * | 1993-10-04 | 1995-03-28 | The Lubrizol Corporation | Mixed carboxylate overbased gels |
| GB9400417D0 (en) * | 1994-01-11 | 1994-03-09 | Bp Chemicals Additives | Lubricating oil composition |
| GB9611316D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611317D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611428D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611424D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611318D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| US6043209A (en) * | 1998-01-06 | 2000-03-28 | Playtex Products, Inc. | Stable compositions for removing stains from fabrics and carpets and inhibiting the resoiling of same |
| WO2005042677A1 (en) * | 2003-10-30 | 2005-05-12 | The Lubrizol Corporation | Process for preparing an overbased detergent |
| JP2014500387A (ja) * | 2010-12-21 | 2014-01-09 | ザ ルブリゾル コーポレイション | 清浄剤を含む潤滑組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB194963I5 (enrdf_load_stackoverflow) * | 1962-05-15 | |||
| US3178368A (en) * | 1962-05-15 | 1965-04-13 | California Research Corp | Process for basic sulfurized metal phenates |
| FR1382559A (fr) * | 1963-02-12 | 1964-12-18 | Lubrizol Corp | Compositions métalliques solubles dans les huiles et leur procédé de préparation |
| US3282835A (en) * | 1963-02-12 | 1966-11-01 | Lubrizol Corp | Carbonated bright stock sulfonates and lubricants containing them |
| GB1044148A (en) * | 1963-09-16 | 1966-09-28 | Lubrizol Corp | Carbonated calcium sulfonate complexes |
| US3365396A (en) * | 1965-12-28 | 1968-01-23 | Texaco Inc | Overbased calcium sulfonate |
| US3493516A (en) * | 1966-05-04 | 1970-02-03 | Chevron Res | Carboxylate modified phenates |
| US3544463A (en) * | 1968-12-19 | 1970-12-01 | Mobil Oil Corp | Overbased oil-soluble metal salts |
| JPS5272707A (en) * | 1975-12-15 | 1977-06-17 | Karonaito Kagaku Kk | Preparation of additive for perbasic lubricating oil |
| FR2416942A1 (fr) * | 1978-02-08 | 1979-09-07 | Orogil | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
-
1983
- 1983-07-11 FR FR8311494A patent/FR2549080B1/fr not_active Expired
-
1984
- 1984-07-06 EP EP84401440A patent/EP0133088B1/fr not_active Expired
- 1984-07-06 AT AT84401440T patent/ATE27298T1/de active
- 1984-07-06 DE DE8484401440T patent/DE3463785D1/de not_active Expired
- 1984-07-06 MX MX27008A patent/MX27008A/es unknown
- 1984-07-09 ZA ZA845265A patent/ZA845265B/xx unknown
- 1984-07-09 GB GB08417478A patent/GB2142928B/en not_active Expired
- 1984-07-09 JP JP59140765A patent/JPS6044595A/ja active Granted
- 1984-07-09 AU AU30400/84A patent/AU574082B2/en not_active Ceased
- 1984-07-09 US US06/628,895 patent/US4698170A/en not_active Expired - Lifetime
- 1984-07-09 GR GR75249A patent/GR81650B/el unknown
- 1984-07-10 PT PT78881A patent/PT78881B/pt not_active IP Right Cessation
- 1984-07-10 ES ES534163A patent/ES8504240A1/es not_active Expired
- 1984-07-10 BR BR8403428A patent/BR8403428A/pt not_active IP Right Cessation
- 1984-07-10 CA CA000458522A patent/CA1217480A/fr not_active Expired
- 1984-07-10 DK DK338184A patent/DK163131C/da not_active IP Right Cessation
- 1984-07-10 PH PH30951A patent/PH20608A/en unknown
-
1987
- 1987-06-06 SG SG501/87A patent/SG50187G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT78881B (fr) | 1986-06-02 |
| DE3463785D1 (en) | 1987-06-25 |
| GB2142928A (en) | 1985-01-30 |
| CA1217480A (fr) | 1987-02-03 |
| EP0133088A1 (fr) | 1985-02-13 |
| DK338184A (da) | 1985-01-12 |
| DK163131C (da) | 1992-06-09 |
| FR2549080A1 (fr) | 1985-01-18 |
| ES534163A0 (es) | 1985-04-01 |
| DK338184D0 (da) | 1984-07-10 |
| FR2549080B1 (fr) | 1986-04-04 |
| JPS6044595A (ja) | 1985-03-09 |
| ES8504240A1 (es) | 1985-04-01 |
| GB2142928B (en) | 1987-01-07 |
| ATE27298T1 (de) | 1987-06-15 |
| PT78881A (fr) | 1984-08-01 |
| PH20608A (en) | 1987-02-24 |
| GB8417478D0 (en) | 1984-08-15 |
| GR81650B (enrdf_load_stackoverflow) | 1984-12-11 |
| DK163131B (da) | 1992-01-20 |
| MX27008A (es) | 1994-03-31 |
| AU574082B2 (en) | 1988-06-30 |
| US4698170A (en) | 1987-10-06 |
| BR8403428A (pt) | 1985-06-25 |
| ZA845265B (en) | 1985-03-27 |
| SG50187G (en) | 1987-08-28 |
| AU3040084A (en) | 1985-01-17 |
| JPH0225397B2 (enrdf_load_stackoverflow) | 1990-06-01 |
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